BE740042A - - Google Patents

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Publication number
BE740042A
BE740042A BE740042A BE740042A BE740042A BE 740042 A BE740042 A BE 740042A BE 740042 A BE740042 A BE 740042A BE 740042 A BE740042 A BE 740042A BE 740042 A BE740042 A BE 740042A
Authority
BE
Belgium
Prior art keywords
radical
compound
product
support
denotes
Prior art date
Application number
BE740042A
Other languages
French (fr)
Original Assignee
Eastman Kodak Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of BE740042A publication Critical patent/BE740042A/fr

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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/09—Sensitisors or activators, e.g. dyestuffs
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
    • C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
    • C09B23/086—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines more than five >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/107—The polymethine chain containing an even number of >CH- groups four >CH- groups
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/485—Direct positive emulsions
    • G03C1/48515—Direct positive emulsions prefogged
    • G03C1/48523—Direct positive emulsions prefogged characterised by the desensitiser
    • G03C1/4853—Direct positive emulsions prefogged characterised by the desensitiser polymethine dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Description

       

   <Desc/Clms Page number 1> 
 



  Nouveaux produits pour la thermographie., 

 <Desc/Clms Page number 2> 

   @   La présente invention concerne des   produits   et des com- 
 EMI2.1 
 positions er::oôr.-ïçue: - : On -utilise fréqueBinent des colorants 1-a=s les procèdes de reproduction thersographique.

   Pour ce faire on imprègne souvent ' les produits d'eT'2'egistre:e:w:t tne:-l:ogra1=hiqu.e de colorants chan-   geant   de   couleur   par   chauffage.   La   chaleur     produisant   le virage 
 EMI2.2 
 peut être apportée p un style chauffante C=4:r-.:-G.:

  .iv par con- tact direct,. ou par une   exposition.   à un   rayonnement   de   grande   énergie calorifique,   exposition     qui   est   modulée   de manière à   former   
 EMI2.3 
 une latente ealorifiquej par exposition au contact d'un do- cument à reproduire dont les   diverses     plages     absorbent   et réfléchis- 
 EMI2.4 
 sent différèrent le rayonnesent calorifique.

   L 1-=aie latente air..- si forcée produit une image visible par   modification   de la cou- 
 EMI2.5 
 leur du colox-mt, saz-s détérioration du document original.. 'Une soxzr- ce de radiations convenant c Ce procédé de reproduction t.'ler::ïogra- plique est la laz>e à filaient de tungstène qui bet un rayonnement riche en infrarouge et en lumière visible. Le procédé therBiogrs# phique convient particulièree."1t bien à la reproduction â'origà.naux ayant des plages absorbant 1-lirfra.-o-agé. Certains des produits thermographiques connus ne sont que peu sensibles aux rayonnements - visibles et nécessitent donc des   expositions   prolongées pour obte- nir des copies acceptables.

   Il est évident que ces   produits   n'ont que des   utilisations     Usitées et     que.,   dans certains cas, ils ne pré- sentent aucun intérêt   pratique*   
 EMI2.6 
 L''invention a pour objets de nouveaux produits the=-==1ographiques caractérisés en ce qu'ils cG:t? eren,co.:.e composé   thermosensible   un composé correspondant une des deux formules   suivantes-.   
 EMI2.7 
 



  ¯   dans     lesquelles:'..'     @   
 EMI2.8 
 R1 peut' avoir une des significations s-:xi:ranss: - ¯ a) -une liaison méthin - terninée par un noyau -hét6ro- cyclicue, du type contenu dans les colorants cyar.ue,px exelsple un des noyaux décrits dans -1-*ouvrage de Hees et Jases "The Theo of the Photographie Processtt., 2-IacSillan éd. , 3ëne éd. .18 232a - la maison méthJ-n po,,ivan i',- être substituée ou non .et étant.,par' ]. ) exesple ime liaison -CE=, -C<Ffl3>1> g= ¯g -CH=C L.3- - 

 <Desc/Clms Page number 3> 

 
 EMI3.1 
 etc i * ** ** * ***' / bu an radical =xw1ià=zcvi-µ-le, tel qu'un radical de formule , . 



  -CH=,^.n ßF33-Côâ, 83 désignant un atome d'.hydrogène os un radical -'' - 
 EMI3.2 
 alcoyle ou 
 EMI3.3 
 c) us radical styryle, éventuellement substituée par exemple.. un radical de fcrcxie -C=C-C6 -, R 2 désignât un --tome d'hydrosene, un croups alcoyie, aryle ou un groups =w1::s, o ta Wen t d4-a2:coylaraino, me! que iijê=hy.1a=>o ; -h lieut, avoir une des sgn2c os suivantes ¯. - ique >-- a) une liaison #éÏhixÉl=#1#ée par un ccyau hété=ocycîique in type ccnterL ds les colors.'s ..=oc;¯î.G, décrit par exemple ¯ - ique ...... r-on .às l'où-v=ace ¯récité, la liaison néthiÔ7=1 .=nt atre Lon 50E5sziàêe 
 EMI3.4 
 ou substituée ; ou 
 EMI3.5 
 b) un radical allylidëca éventuelleneui substitué, el qu'un radical cyanoallylidè1:.e, un radical alcoyicsrboxyallylidee eu ç3coylsuL oy?alïy'¯.idëne ; 
 EMI3.6 
 'Peu désigner:

   
 EMI3.7 
 a) un radical a1co;(!-e x3' z avé1:;. t.;",s"'me!l't de.1Ul b. hui-: atomes de carbone, tel qu'un radical =ézhà-1e, proxyle, éthyle, cutyle, etc,ce radical pouvant être substitué, étant par exemple un iai=cal sulfc- vlCGflG-9 tel que le radical -(.'SJ3 , un radical aryla1cDyl5, par exemTBßJle un radical bE."1".c.jr' !By or un sel par exemple -(cE )¯-J-1 , Y désignant un sel de pyrr¯w:.¯u. substitué ou non S1.1us't:l.tu.e ;. z, un radical acyle, par exemple -C(Ç}-:a4 où ' G3 un radical alcoyle z3. 5 avantaceusenent de un à huit atoces de carbone ou un radical aryle, par exemple un :radical méthyle, 67Zby'te, propyle, bu;.y:.e, phényle, aap ;r e, etc, cs c) un radical aryle éV(1:..e2.1c:::

  ent substituée tel 'lu fun radical phényle, naphtyle, s zo-y3e, etc Z représente les atomes nécessaires pour compléter un noyau --étéroc,vc!4-,C-,ue 2 cinq ou à .six chaînons, ce noyau contenant 

 <Desc/Clms Page number 4> 

 
 EMI4.1 
 au moirés un atome autre ,Clu"un otoxe de . Carbo:.e, :.el ÇU'1.ln .atome doÀ7;!mc" de soufre de s,rlén1t.:.::1 ou d''ao4e,Ce noyau tt:.."'1t"par oXeYle,L: noyau pyridinc##### uir.ol1e"ec;

   X .rercsc.:.e un anion,tel QUI ax:ica cfào*1=-e, broure,o- de"?orch1orte,,sU::ta, =oc;a.:: e,,sr-to:.è.e sw..3.'onate,, i:3E.''47;jJ.Sl.'.1 :."rf3, viiJ F.:.tii;0 09.OIF.' 8, e Cj Les CO05'S ê6ir.ls 6sentt us ense=10 de propriétés qui los rendant utilisables dans des procrz'dés Jt-.re7s divers d'obten- .tien d'wa,es.Er décoloras par la chale1 ils so: , =..-e;r, 3 ut4oÀisies en ,,re wa;r,::.e., ce ç#1 est l"objet de la présente / 
 EMI4.2 
 demande do brevet.

   On peut préparer les composes utilises suivait 
 EMI4.3 
 l'invent1on coe==e décrit il la de=---.de de brevet belge n  78 51t6, déposée le 29 août 1969 au nom de la Demanderesse. i Les composés dfin1s ci-dessus sont ch1=ue altères quand on les soumet à bzz c."'1auf.f':lge,;.ar exemple à la chaleur appor- tée par des radiations 1r.rarouges.D'tLe  ,':'I;t:2'8 cé#é=a=1e,cette L"i''c,'r c":'v...'OI3 est u..."':. coupure de la :::ollcule,do 1,: ..'.C,::.8."..E.' précis dépend du compose précis utilise.

   Ce 1tÉcx#isr:e ..-....-.1'... a-:J,.....c na- niere 1"'.....1....",,! <'> nr>a.. ""'''.) au SU'h''''''''.a. "'''''1''" sur an exemple particulier: . i --.-'" C e 
 EMI4.4 
 
 EMI4.5 
 La èLc.Qh.. -; O:l x- l'actio; Ga- '1-at:.i'.:téffa- i?;-ft- &;;.te::.ue- :?r- CO.P htL-'Y""l'q"C c.'c la .. "of O"" de 4 .:e à o""'-"'7" ion 14q.D+et %,-ne base V l1oo4o .l..¯c.;....;.;> ¯4 ..,éC S$ Y'c':-a.^..:s.L' -"'-'\,;- "--- ...... "'.....L... e ose colotc qui eut =e ±rcte è4V;1tage.Cest iette . base cJlon-nta çr' est "ilis6e 1>ohte=ticn d'iges.Les '."';-1""5 !'---",-"'- -o..,,"....s la cO"""" L'.C.' -.^w ¯-1,..,o :,""'vc"",:- re ,.

   Pro"-- éZ*.Orce-- dive-zes reacl--'ons i rue '1 'ïSt" ou la .a.. o wi r..t ..1 - ¯.- "!a -01,,-- tso OU l r6c:o. cOuer oina qse le # d-a ap- =..:':n t C:;':2.d 0:1 e t<.i te pr 1.:-, acide dc- :::a.,ièc; cue e ;3. du. ;;:;:0- .a  soi '#Sé=' n= ± 7,-às ne ",:1. ""'-".....1.. '-' :)zz ç- v...:..:.....:;,.",,- C,7,lZe C-,Za--4d ='L' coo-"" GSi.

   J,'l:a.d <'I Z¯cCw L't'iZ''3C' ...r'''''''''''e a4CWi des frh:;;::e::ts ,;.t:'Oc:uits WW.4r4' de Va.rY'v'1.J4S ièes: 

 <Desc/Clms Page number 5> 

 
 EMI5.1 
 par exe2e,Ia? d;.e est un agent efficace de ré4.-iculation-ët-- 
 EMI5.2 
 un mordant de colorante les radicaux libres et les cations sont 
 EMI5.3 
 des initiateurs de polymérisation. " ".; Suivant divers sodés avantageux de aise en oeuvre de 1-,:Ln- veion,a atiise des composés theraosensibles ca:fa es à la dé- 
 EMI5.4 
 finition générale donnée ci-dessus et correspondant plus parti--- 
 EMI5.5 
 à une des forrules suivantes- ' ¯¯ ,¯ , ¯' .] j 
 EMI5.6 
 ¯ ----r-GgTC-s-h--a-s=GE---'-E3 g n-1 - 1 . 



  2 .. OR ¯ . -- -I- = - i= - ' ; ¯ .fl "rut oy " l', ¯ ' - Î '/ 1 . R-l ±¯,¯, OR E . ¯ D . - - ; . ''.: R2 ,,. -qÔi]=?= 1. fr ¯ , 7% / "' é ¯- ' ¯ ¯ ¯ ' Î - C) =c3-CH=?=C-#L=L--G ô., ¯ ¯ ¯ - ! - S-l ¯ n ' , 1 1 ...1 -" X . ¯ ', ? : . ' " = -, .- .. ? , -=E2 .", "- <; . ' " Î( ' 'i "   " ..;.-r'X - -. ¯' ,lli"Ù"Ô/; . ,,-Q?/ ,, -Q?-,,, - : - : D) .C ^'it-s-=s T r tr â Y iT:' 11 .   -, ; -] / .. g-1 .. ' - . -s ' ' ¯ - " ", . ¯ . - ,... 



  - :-/''...L.;-¯ " ' ÎÎ" j . " V 1" / 1 ±"$ -;2 OR 2É ' ^ ¯ -q2 1 ! - ' - ¯ f " s bzz 2 ¯ ¯ ¯ µ, -Q2¯ nY ) - RO-N--SE=CH:--C==L-L=5=C##&=0 ou. g-1 m 

 <Desc/Clms Page number 6> 

 
 EMI6.1 
 
 EMI6.2 
 5>"Dans ces i'ornules; les 'symboles ont les significations suivantes : ¯ t, . - . QI, 'Q2) 'Q3, e Q9 représentent chacun T.es atomes 5 non méta1.iques' nécessaires pour compléter un noyau. sensibilisateur . . ou désensibilisateur comprenant 'Un hétérocycle à cinq ou à six. ato- nes, dont au coins un atome autre qu'u..'1 atome de carbone, tel qu'un : .' atone d'oxygène, de soufre,, de sélénium ou d' azo e, c'est-à-Çlire un 
 EMI6.3 
 noyau d'un des*types utilises dans la préparation des colorants 
 EMI6.4 
 - cyarii.ne? tel qu'un des noyaux typiques suivants :

   les noyaux de. la fani3"1 e du thiazole, par exemple les royaux thiazole, 4-methylthia- " zole, 3-étly?thiazoles 4-phb..y1thiazole, 5-::1éthylthiazoJ..e, 5-phényl-. 



  ¯¯ thiazole, 4,5-din:éthylthiazole, 1:-,5-diphé:lylthiazole, 4-(2-thiényl)- :. thiazole, benzothiazole, 4-chlorobenzothiasolej 4- ou 5-nitroberso- 5 tMazole, 5'-cJ>..lorobenzothiazole, 6-croro erlzo-::::-.d.ê.zo1.e, 7-chloro- .' benzoNùiazole, 4-nétlflylbenzothiazJle, 5-éthyl.bB:lZot:rlazole, 6-mé- .hylbenzothiazo.e 3 E-r.4r ooertzo .aZOIe y i-bxraàbenza L:.;a.zole, ¯6- bronobenzothlazole, 5-chloro-6-nitrobenzot;hiazole, 4-phénylbenzo- - - thiazole, --é,oxyberzzo4biazo.se, $-wéboxuenzo=.àaza3e, 6-méthoxy- ) >benotiniazole, 5'-iodobenzothiazole, 6-îoiôDenzotàîazole> 4-éthoxy- .é benzo 4'..'3 azo'' e j '5 -é-::::J.0):;Tbe'2;ot;-iaz01...e;) ,'-.T x ay 4 oie¯'ïzo V âsazo.e 5,6- d:é ¯oxyberzo'^..azale, 5,6-zéthylène(ioxybenothiazo?e, 5'-?ydroxy- -benzothiazole, 6-hydroX"j'benzothiazole, a-naphtot1-..iazole, p-naphto- ' -thiazole, f? .1......, . l $-cL:

  oa..s3¯napoLziazo?e' "'...... f? hL .1.hi . "1 8 "o..' . "'t- .;..' , 7 "t" , t P-naphtothiazole S-setho-x-naphtotasole 7-r4thoxy-c:-naphto- thiaole, ':'-vé4bcx,ynaTaphc:o-;'a6',=,$-û-:iazo?e, les nitro- napboz.aLo3es, etc. ; les noyaux de la (x#iî7e de 3.ja:azole, par exemple les noyaux 4-sethylcxazole 4-r tro-oxazole, 5-;:;.éth'loxazole:l 4-phenyioxazc'le) 4,5-diphényloxazole, 4-éth-yloxazole, 4) 5--diJ":1éthy1.- }oxazole, j-pbény.oxazoes benzoxazole, 5-chlorabenzoxazole, 5-méthy- "tsenzoxazoie, 5-phénylbe$oxazole) Ç- ou 6-5±trmDenzoxazole, 5-chlo,-.. ro-6-nîtrflDe;zo>azole, 6-=étlÉyînenzoxazo'e> s $, S-di ê hylbenzoxazo'i e 5 . 



  3-s6-diéL :y.benzo:azole, 5-méthoxybenzoxazole, 5-t:c.o7-Yben2oxazole, 6 tëboxßoe:2oxazoie 5-hydroxybenzoxazole, 6--ydâohybenzo;zcle, ,oe-na>htoxazalg, p-naphtoxazole, les divers nitro naphtoxazoles> etc.;. les noyaux de la fasille du sélE?:1azole, par exemple les noyaux 4-!:1éthylsélénazole) 4-;-li. troséléI".a.zole, 4-phénylsélénazple, benzo- : sélénazole, 5-c::ù.o::-obenzosélénazole) 5-méthoxybenzo5 élénazo1e ; ,-hYdIoXYbenzoslénazole, 5- ou 6-ritrcb?nzo<élénazole 5-chloro- z 

 <Desc/Clms Page number 7> 

 
 EMI7.1 
 fi-nitrobenzosé3énazaiei 'éir,y3=ôcenzos2?énazQîe, ocaapßosé3én-- ];li=q¯. âoïe, I3-naphtosélénazol, les divers nitro naphtoséîéna'zo2esß etc ,r> - - ::-- les noyaux lie la faaille de la 1;hiazolÛle,' par exemple les noyaux¯ thJ.azo3ine, -ét.''.,-,1 iazaline, etc ;

   les ncysnx de la Manille de ) la pyridine, par exemple les noyaux. 2-pyridine, S-nè :hy2-2-çyrid.iae .. ¯ ¯ 4-pyridine, 3--thyl¯4 y'='iàine les diverses i-tra-p-,rièi:.es, etc ;' -' , les noyaux des familles de la cuincleine et de 2';soçs::.oîQi..ex par - exemples les noyaux 2-quinoléine, 3-méjy1-2-qu±noléhne, ¯$--éhy1- 2-quinoléine-, S-chlora-2-çu.nolée, 6 i:ro-2-çuJ.no3iae, 8-chloro-" 2-quinoléine, 6-xétoxy 2-çzircïéi¯^¯e, 8-éo uinoléina, E-y- Q 3roxy-2-ç::ixozéine, 4-quinoléine, 5-.:.éLo--çuinoléine, 6-nî=rc--4- quinoléine, 7-néthyî-4--çnirolé>e, ô-chio=o-4--quiw1oléîne, 1-isoquino- léine, 6 xißro-'F-iso;uo?éine, 3,.-3i;y-a-:-isaçuinoîéi:ga 3-iso- - quinoléine, etc ; les noyau.!: 3,3-4iaîcoy? i:.dcla, por-:ant avata# geusesest un suostiTxant nitro os. ,a:

   o, 1;e:B f;;.ua les noyaux 3,3-di- zéthyl-5 ou 6-niz=oindoiéirn, 3=3-di ;G-t'.^iyl -- on 6-cyanoindolé!:ir.e, etc ; les noyaux de la famille de i'¯d22ate, par exemple les noyaux, imidazole, 1-alcoyli=iàezole, r-aiçoy?-# péaylir..ic.azole, 1-alcoyl-4,5-diEétl!yli!aida=ole, aaz¯..^.¯3azole, 1-alcoylbenzi::.idazole, 1-a:co;l --:it=oenûiidazo'?e, -:yï-1a6.ic'-.îorGbenxiidazo3e, 1-alcoyl-x-aa?htidazoia, i-y?¯ï¯na,4i:.da.o2e, 1-alcoyl-5-cé- T.hoxy-o#naphtalisidaz&le, les noyaux de la taieille de l'iidaso4t5'-37*' quinoxaline, par ±-.xc,i=e les .:Gy-u.'.X I-#lcc'i=i3==of4,jfflc#±-oxaii=e tels cse -ô-ézhylinida=of4,5>flq'aincxaline, 5-chlo=o-1-ê=±rlir=Ldazo- L y5-Jçsincxa3i!e, e:.c, 1-Q.lc:::y li-::d.dazoL 4, 5-Êl quinoxìr..o,.p<::r' exemple 1-al$yliniéao±4,p flq'iGox=lî=o, 6-=h'oro-1-<-lylimidazo- f4,> flçuincx=l1#e, 8'LO, ;

  -a=iioi#zoS4,pflquinoxàine,  =r exemple '-gény îî :3azaL , --ç''oz<<iaes 6=Elo=o-1-pEé=zriinid==o- L 1, %-guinaxaliae, e ta les noyaux ., --àia.'.coy3--3 Lyrrol a,.î-=?7 pyridise, par exemple .î,3ic.étî-s.¯ F'rraîc, Jp:fridine, 3,3- d:.é'L:ß 1-,;ß;%.T3'OiGL 2-,b %p;'râa, été ; le :::oya-a 'thia.zcloL4,5-ÈÏ- 
 EMI7.2 
 quinoléine, etc , 
 EMI7.3 
 R3 xep=ésente gnoupe ., , ... 1. - représente groupe -coy.e êventnellesen'. uas'..i'.éj avan J;as6use:;en't un groupe alcoyle inférieur, c^.y: . ::::.a1;ra a%C=e3 de carbone, par exewpîe un groupe mêzhyle, ét:yîa, propyle, isopropyle, cu-tyle, hexyle, cyclohexyle, décyle, dadÉCyîe% e1;c, un groupe 1;ydroxyc.lcoyle, par exemple p-hya-ozyrê*yie,L3/ny>oxàJ.aty?e, etc, un groupe alcoxya.lcoyle, p<-X" exemple #mêTh.oxyêthyl tal #buto.xy# ÙàYle,' eta ;

   un groupe ce.=SOcorie.- - ¯ exemple J3-c.arbox;)'le, kà-czflooxybutyàe, e t; , un groupe alaa-j, par exes-############ 

 <Desc/Clms Page number 8> 

 
 EMI8.1 
 pie m6-t-oxy, e.za3xy etc, , -un groupe ...t.:... : :- :5.-.'.à.â: ; par ...",,..-....1'" --''s..'..'C3± :y s.é-.fi. s.:.':7,.'s3:.=. .2 g L C. y, 'c:-= ,t;.: :' i " â.':'c;.:::.¯''..Ci;f â .B par O:.............."".....-:3..t....... .....- û.'s:EI?¯ :r .'''. ',r"....w.... ..â..' n ? p2.r L3'.,.::. ..:' fl-,=5-. tlaox3rcai=->lé=1=;.1< , -;1-àt±=ox3rca±Joylbutj-1*, c-tc.

   C..- t;. <";y':..:p7;' a"EZ- 'C;r'.e?. par exe::?:e.., i.<iy6 p1:é..:f;;:yle, otr, 3 . ;::j::;,i: ::".:::;1; pas  : 'é..'..C .1#y#& 2-pop;:yle, 2-jaté#3.le, y tJ: :.'. c'n. in :;-=;:; ".;' a a==il± ¯ xà> CL'j..B3 i.^ 7:,.' tc1.y2e,-?::.tyle, é::.o""?:::::r2:) chlo=<:#3=5#1.'lc etc. ; bzz¯ 1'$â. ' eSc .:,.eS a ' â.O.A'..5 : ^v' w':. rt,.?....j..:. ¯t ' M.: .,'' ::: s=t'..

   S Ss. ¯ L'sr r30'.:" #&reprqsërLt& les atomes .ncs L-- =..cessa.ires; poTir 'il. :r-e²'- sc::¯ les atones 4";""-" ::;;:",...¯--.....;:...;;:\,..<;;;$;;.",-- ).J- ) compléter 'u a1Jyau héterocyclicue à cinq ou s>= W.4 s CVwaVÂ^KsirV suivait 'r'  1% exemple i "Un j' MÇ1 è..'i:lzote, da sv-:re..s.±6¯- {.,,",, ;;'o'Y""VC- ,,,,,, 3^1 C'"'''l''''' 'n'f -u-"''''-''' 2--"'-"""'-c"':'::':"'¯-0-:- I.'-"""Z;'" e",.",",,"'P"I,1e ni% on d oxygène, tel ,.\.4. "--i. noya-n 2-P =a..cw¯ --o ::: (p3.r exemple L t.:',.- " i.:y 3.-G"" a's?.T.r.....; :"' tÂâ.f'.' w"'.1 :L': '..."'"' rt c,..".Û.r: . -t,i. 



  't¯2-2 :.."ov:.:.2: o?y'! i- i-: Cyi¯?- .Oz¯ :-j-s :y etc.); g noy .'fJâi'.82'.o.¯O:.± -...... SÂ'..".."r.. .4 y - :CI"".f..-! 1:.' f  = 'Cf. .. L...O¯ .#. 3-ethyl-5'- tE)-isoxazo!or.e2'etc); 2L7. S:Oya;x O:i:..û:C.' (;r exemples 1-alcoyl- 2 , 34ihyWàn-> j-2-o>ii#à+le . eta. ) > rxn -....." w. :: (. 4 ¯.v s;a v; j r ... tel tjLi. 1,'... radical acids barbiturique ou acide --;::.:.oa:-::'i.t1.:.iQ.ue por- tant éventuelle=ent àos substitus-nts 4a'.Yoi.L4W..i position. 1 (1 mi4Lriy 1-propy2-, 1-hepy? , etc.) ou eu positions 1 et 3 (' y 3-.;: ét:yl-# . 1,3-d.éthyl-3 ? s.i-cip=ePy.-y .s3-üsopro=yl x =-::iyc.o :e:f.-3 13-di(aethoxycthyl)-, etc. ou des substituants û f.'..

   L'1 position ,3.- P ÎIGIi Yl -s 1-?-chlorc>hé#ylL, 1-p-ét2:oxycar'!:lo:::tlpényl-, etc.)'ou en positions 1 et 3 ii,j-àiK-1é;yi-, 1$ 3-di {p-c :10= c : r.yl-, 1,3-di- (p-élhoxyçarboy1pényZ-, etc.) ou un substituant alcoyle en posi- tion 1 et 'm substitca;t aryle en position 3 (1-éthy3-3-p:nyl-s 1-n Y.epty3-3 hû:yl-r etc.), tel qu'un noyau rhodanine (c'est-à-dire un noyau de 1 fa=ille des 2-tb-t-o-?,4-th4azolidinediones) , tel qu'un noyau rhodanine, 3-alcoylrhoJanine, (3-éthyl-hodanine , 3-allylrho- danine, etc.), 3-carboxyalcoylrhodanine (3-(2-carboxyéthyl)rhodanine, 3-(4-carboxybLtyl)rhodanines etc.), r-suloulcoylr:aodanir.e, (3-(2-sul- tothy2,rhodaa:iz:es ,3-(3-sul2opropyl;rhodaHi.^.es 3-(4-sulfobutyl)rho- danine, etc.), ou 3-arylrho:anS.:e..(-P;nyir:odan.ine, etc.), etc.;

   tel qu'un noyau 2(3-iaidazo,'12-pYriàa:e ou 2-.fu:-anone (3-cyano- -phny3.-('Ej-turanones etc.): tel qu'un noyau th=o.i'.én-3-o:xe-I,1- dioxide (benzobthioghn 3(2i:-one-lsl-diox.ide etc.); tel.quun aoyau ,,7'âiOXO-b,?-àihy dra'-thiaZOio ,r3f2-pYxiuidi:.e-(a?-d3.oxo- . 



  3-IAYl- s?3'3xo-$ iziazolo, 2-Pyrinidir:e etc.), tel qu'un ioyau 2-thio-2,4-oxazolidinedione (c'est-à-dire un noyau de la fa- 

 <Desc/Clms Page number 9> 

 
 EMI9.1 
 ........... ui"e de 2-t:ûc-2'-r i3=:.-Î-03.'az0¯''iU':U'$:é.=::':f:2-thia-2,3--ox.- zo1iàOedione, ,3-C,2-s:.Qéthy33-2-thio-2ir-oxazoLidineaione3 3-(4- sn:Ic,utyl)-2-t'hsa-2,--oxazalitin edior.e 3-(3-carbo3rypropyl)-2-thic- ¯ 2t-oxazol3di.ed;tr.^¯es etc.); un noyau thianaphténone (2-(211)-thiana. phtenone, etc.): sel qu'un noyau 2- t h io-2 5-th.îazo2dinedione c'est- fi a-dire de la faaiile &s 2-thio-2,C3H-ï')-thiazo?ec.iones) (3-éthyl- 2=:.h.o--t:îazolîdinedîOn23 etc.); tel qu'un noyau 2,4-thiazolidir diona 2jt-t:.i.aza'¯idir.edi one 3-éthyl--2--t â:.azolîdi .ediones 3-phé-¯ nyl-2,4-trazolidinedione, 3-a-ryhtyl-,-thzazolidinedione etc. );

   tel qu'un noyau tiazc3ici=none (4-thiazolidînone, 3-éth7l4-thiazo- D lidinone, 3-phényl-4-thiazolidliione, 3r.s-naphtyl-4-thiazolldin.one, etc.); tel qu''1 noya 2-iazolin-4-one (2-É thy? rercap to-2 thia- zolin-4-one, 2-alccylphénylanino-2-thiazolin-4-one, 2-diphénylamino- 2-thiazolin-4-one, etc.) ; tel qn'nn noyau 2-inino-4-oxazolidinoae (on) psEUdohydaitoi^2) tel Qu'un noyau 2s-iidazo?idinediane i (hydantoïne) :23-iiêazalscinedio:e, 3-éthyl-2,-s--iidazolidi.ne- dio#e, 3-phés.yl-2,:--ir.idazo? idir.ed.one s 3-a-naphty3-2 --iidazoi.- dinedione, 33-c..>ûhyi-2-?idazo?idinedione 1-éthyl-3-phényl- 2,"-1:xidazo'iài,eài=n#, 3-éü;=.-2-x-naphtyl-2,--iidazo.idinedionei 1,3-ûi; :

   enys-2, -,a.aiû.c'3ZOt?.cl ned:ion e etc.) , tel qu'un noyau 2-thio- 2,4-imiàazoliéinedione (ou, 2-tlaioànydanto]ne) (2-thio-2j4-imidazo- lidinedione, s 3-ét :y i-2-thio-2s-i:i dazo? idinedione, 3-(4-sulfobùtyl)- 2-tliio-2,4-iidazolidi.edioiie, 3-(2-carboXyethyl)-2-thio-2j4-inida- zolidinedione, 3-phényl-2-thio-2,4-imidazoidinedione,-3-a-naphtyl- 2-thio-2,Y-iridazolidinedione, l,3-diéthyl-2-thio-2,4-imidazolidine- diane, .-ét:yl-3-phényl-2-thr o-2,Z:-iidazolidinedioney l-éthyl-3- rô.p.ayl-2-thzo-2,--iidazolidirsedions 1,3-diphényl-2-thio-2,4- z imîàazolidineàione, etc.) ; ou tel qu'un noyau 2-îmidazolin-5-one ;

   (2-prohylmercapto-2-imidazolîn-5-one, etc.) ; -- n est un entier positif compris entre 1 et 4 ; ; - n est uns deux ou trois.; , . g 6 est 1 ou 2 ;¯ * j R6 et R désignent chacun un radical cyano, un radi- cal ester (éthoxycarbonY7 néthoxycarbonyl-, etc.), ou alcoyi-sul- ¯) rony1e (e:hylsuli"onyl-, éthyisu3iony? -etc. 3; ---- - - .- - -#"""" - L représente une chaîne méthine de iormlxle #C= ou.

   T " 2 , ¯ ¯ at un atose d'hydrogène, un radical alcoyle ayant de 1 à 4 atomes 
 EMI9.2 
 te carbone ou un. groupe aryle (phényle, etc.) 
 EMI9.3 
 ,"¯, - I. Î,ÉÉRtBÔÎ/nÉntlllÉltàecs .*.. - D, E, J, R2 et R4 désignent indépendamment des atones . 1 ..... .. ¯¯ ::''..- . -- 

 <Desc/Clms Page number 10> 

 
 EMI10.1 
 d'hydrogène, des groupes acoyie,content av.nt.t;weusent de 1 à 4 atomes de carbone), (méthyle, éibyle, propyle, isopropyle, butyle, décyle, dodecyle, etc), ou des groupes aryle (phênyle, tolyle, naphtyle, méthoxyphényle, ni-.ro-ah,64yle, etc) ;

   X représente un anion, (chlorure , bzo=re, iodure, perchlorate, tatrafluoroborate, thiocyanate, p-o2zè:es sulfoste, stêthyl# 
 EMI10.2 
 sulfate, etc) , 
 EMI10.3 
 G rapréser¯Le un r4dicl enilino cn Lrzle, (n±é=y1<, naphtyle., diaiccylsinophenyle toîyle, oIorophênyï, >z=z=ojhé=yie ailinsvinyle, 
 EMI10.4 
 été) , 
 EMI10.5 
 =ep-é;ente raiix=1 -1.=;j.Il#escy - représente un radics.1 ####### .,.. 4 .GÜ:ßt syEn'= t.'.'t1â '.0.^..23 de C L7Gae dt-ns la ebai## 12:cy,1-.:- .. =n =iàic=1 l's'. 'w :.a for='..Ie (C' ) -.r;? éns- (Cn; - -C, , eu L 2a *.#ioi= i à 7 2, tel culun K* fa ¯ cri, zét=z-=éthyî- eneoxy, ;rox3.liààneaxy, étl'.L&nedo.xy, >=é=y13;-ùhi#ézEoz3", etc ; e - 2 nep=é-en2e aoi:

   un =aiic=? alcoyie. éventuellement substitua, - aya#t =v==t=ceuzi#i=I de un à quatre atomes de ca.rbcne, tel qu'un radical nsthyle, ethyle, propyle, isopropyle, buty'-Ie, hexyle, cyclohexyle, décyle, d0C''.ÉGjl$, un radical q7.i'un radical censyle, un medical sulfoalcoyie, xar exemple 6-sulfoëthyle, #sulfo'butyle, #sulfopro'oyie, soit un radical acyle, par exeMple un radical de formule -C(û)-3 où Ru par exemple un ⯠curz :ézh5>¯e, 2myle, napn ß le, propyle, be :¯:, etc. 



  Dans les formules précédentes, Q2 représente de préférence les ator-.es nécessaires pour un noyau pyridine ou quinolêne, D, ez J sont de préférence des zldio=x aryle. 



  3es typiques de colorants décolorés par ---a lumière et d'internédisires pour leur préparation sont les composés suivants : 1. perchlorate de 3-ézhyl-1'-méthozyoxa-2'-pyridoc==bacyanine 2. tétraßluorobcrae de l'--éthox3r-3-éthy?qza=21=¯pùridqcaTDocyznîne ioduré -le 3'-ézhyl-1-néthoxy-2-py=idoihî=cy ine 4. técrdluo=obo=ato àe 1-éihoxyr-3'-éthyl-2-pyridcthiacy==1nB iodure de 1-benzyloxy-3'-éthyl-2-nyni-ioil-iacyaz*ine 6. indure de 3'-éthyl-1-xélîoxy-2-py=ido=hîac==bocyznine 7.. zÉ :,ß aï? ucrroborate de i-éthoxy-3*-ézhyl-2-sy=iio=hiacarbocyanine 8. bydrcXy.de de anhyàro-3'-*éthyl-1-(3-sulTo ropoxy)-2-Qyràào=hia- earcocysnine perchlorate de 1-T:en2yloxy#3'#éti!yi#2#pyridothi.aoar'bocyanne in, perchlorate de 3'-êtl-1-aého-2-pyridothiadicarT:ocyanine ¯¯¯¯ 1t< picrate de '!'#mêtho2y-1,3!3-trisë'):

  hylindo-2'#pyridocarbocysnine 

 <Desc/Clms Page number 11> 

 
 EMI11.1 
 12. perchlorate ae 3T-e; i-eyuor,-ç?7--nenzo-c pyrzaozacaruocyanui 13. tétrafluoroborate de !-éthox-, 3'-étQyï-°' y' benza-2-pyrido- - - . ": thiacarbocyaninë 14. -:étrafluoro'bora'te de .l'-ézhoxy-3-ézhyloxa-2'-czbocyenîne 5 15. tétrafluoroborate de 1 '-é;hoxy-3-é;1 hia-2'-cyani.ne 16. #é =IIt02'ObOr a:e de T-éthoxy-3-ethyl?hia-2'-csrbooyanine 1?. :éi.Z'<zW.OrCJOrôwe de ?'-c:.'. .Cx;f--..z'yv:2â-2'-.'.WC r:/OCjI '13âI6 :. 2CL:.dnZe- G6 ?-.'^"w¯LSYßr-'-.'e..j'i--#.i-".On.ir.COir.

   O:'û"bOCy7.33g ':9. perchlorate de 3'-éthy-j-cXY-4-py=idoiacyine 2J. 'r''¯'2 C.'.J.CrfiW.' de 3'-±' .r'i-' c: #¯:O,f-T-Jy =1tlQ i.'.".lâCnT'ûOCy cwj.:uB 21. mémr=ii;o=oôo>a=e de ?'-é :=o.ay-3-éz=v'j-= s u-oenze G' :=bocyanine 22. p-o:èè-31:ot6 de 2--w...¯inovi..zyi-?-xétozy:;f diui; 23. aerérhlo=ate de i-é i,i-l'-:.é .:-r- n j?=oer.zo ; 4w .'-c-. âocrrins 2L. dibroin-ire de ''-tz,',rl2ci..'.OX',/Dl5Dj2:..^înil:IL1 25. 3bro:.,=re de ï=1'-=ixéß:yiue.iu-3lazs#yridir'¯..... 



  26. d..'¯D20. 28 e 'ii :"ßc=:G :"vïs: cr.30Xj%335-2 wéT.;%1..72ciiti. 



  27. dibrcsnire de i, i'-érawé;"vlë:e-,.;oxyhis(4-:.ct::ylpyridiniua) 28. d-bro=-tre de 1,1r-tét=aétsr.6ioxYDispy=idinium 29. dibro=u.re de ?3?'-pen-sét:;,r.èna^.iaryioispyri4iaium 3C. perchlorate de 1-acétoxy-2-(4-di=iêtBylasinostyryl)pyri<iijiium 31. perchlorate de 1 enzayßcxy-2-;#-âi.ét:^,,vla.:.inosvyryl)pyri in¯u 32, #...,..^..8 ' s.": é .:y --e- S s-  é .t.GT-2-( ij--yr¯dyi.déne j W<.y<i4én 2-thiobhi ruriçue 33. :,-éi'i-l-(?-aëhox3--2(?::j-Yyri.;l3dènejét?ylidè:¯% ho,.e 34. acide ?3-âiél--(?-écr,f-2('13-pyriôyy..idànaëßh;3idén ba--bi-.urique 35. t3, 3-3ioyaaaaliy2idër.e - i-wé ;.: oxy-?, 2-drâropyridins 36. 2-%('-xét.'.flx-2( ?E) y rid;,: ièsre-é iylidènbenzor #}.-' opEëna- 3(2ù)-one-1,1%-àîoxyÀe 37. 3-câa.' o-- r ( 3-ë :'aox,Y-2( ?E;-p,r iây3¯3ëne j é ts:yiïdèn-t é:,'i¯ 2(53)- u=anone. 



  Les colorants définis c:,---dessus, plus pa=zicnliêrezent ceux qui correspondent â une des formlles A à H, peuvent siù*x1i= à obtenir des copies thermographiques de documents. Conne --51 a été expliqué, ces composes se fragmentent sans 3' ac iax de la chaleur et perdent leur 
 EMI11.2 
 couleur initiale : généralement, ils se décolorent, ce qui permet de 
 EMI11.3 
 Les utiliser comsie produits t1:ermosensièJ.es. Les composes foraant la partie photosensiole de la feuille 
 EMI11.4 
 Le reproduction peuvent être déposés en couche sur un support ou meuvent imprégner ce support.

   On utilise plus particulièrement un support 

 <Desc/Clms Page number 12> 

 
 EMI12.1 
 ."<'*%* '1 "' <' t ! g: z "'é" ..... -1 ....... ttillsar ' ' ayant une faible conductivité thermique 06nerueAl8nt, n poil utiliser un papier ordinaire comme support d'une composition et papier .,potavant être transparenty trluc1d. ou opaque. Il est fr4quea- ment souhaitable d'utiliser un su?port qui transmetta les rauoations 4.:-d:.\innt l'expoaitian particul1l1rement ai l'original reproduit ast opaque pour 041148--ci ; au moins une des daux feuilles (original ou feuille de reproduction) doit être transparent* aux radiations utilia6.s. 



  Il ..'1 avantageux rue la support uti11;., aotacexnt on papier ou *n autre produit floraux, ne commence pu 1 se oarboaisar avant )25*C 
 EMI12.2 
 environ* 
 EMI12.3 
 Pour p-psrs: les produit* twerograpkxçuss suivant l'invention, on dépose généralement un* couche de ooloraat ther::i08naible aur un support opAQue ou tranlSluoide. J.'p:a s,obA[;Q, on plaas la feuille de reproductioa au contact d'un orisino: oontenant des lignât, par exemple nn tsxa tnpé la machina à et on exposa 14 tout à des rad1a- tio*=a 1ni"ro ougoa..

   Ias pln"^^es du docutMnt ri reproduire qui absorbent beaucoup les rayonceaects infrarouges tra.,rsa: orsaen: ces r&.yor.n.men ex chaleur, qui oai t:s:.siss à lys. :e::=îîa do copie, ce qui produit rtpidex-Mt un ciànùexext ào aoaloa= :10:..11 140e plaé-os de 1* fouille de =*px*oiàctio= qui son: en =ag=1 des P::';1'''U$ ab;o=bant la chaleur du document à reproduire. lea places de la feuille de copie qui ne sont pas en rc$<.rd des ditee pl. du doo#ren= y....^.::::.;.t oa: r'1cson les :.-...iiutl.0:'4a 1ni'ra:rot;ès, si bien qu'il re soe produit p.: de xodifi- cation da couleur. 



  Si on le deairw, un peut w.cpCr.:er les aaxpoada therxosea- 

 <Desc/Clms Page number 13> 

 
 EMI13.1 
 ,l's1hles dans un liant et. déposer sur le support une couche de -3a :'-'a;; # : composition ainsi forsée..Parai les liants appropriés, on peut citer 1-léthyl-cellulose., l,alc6or-polyvL-iyliqile, la ,gélatine,, le co2lo-V dion, 1 eacétal- polyvinylique, les esters cellulosiques, les esters ? cellulosiques hydrolysés, etc. Quand on utilise un liant   collol-   dal, on peut faire varier le contraste des copies obtenues en   agis--   sant sur la quantité de liant.

   Ceci est bien connu des   spécialis-   tes.   On   peut obtenir des effets esthétiques divers en   ajoutant   des pigments ou des colorants inertes aux dispersions colloïdales, bien   qu'il   n'y ait généralement aucun avantage à le faire. Dans certains- cas, on observe un accroissement apparent du contraste en introduisant   un   pigment colorant dans le liant colloïdal. 



   La source de radiations infrarouges peut être disposée pour que la face postérieure du   document   original reçoive le rayonnement, bien que, dans de tels cas, il puisse être opportun qu'une surface isolante soit appliquée contre le verso de   1''original   pour locali- ser et intensifier la chaleur reçue par cet original. On peut 
 EMI13.2 
 aussi suivant une autre di:sDos - 4 'ion, t, placer la couche thermosen-   sible   de la feuille de reproduction contre les caractères   impri-   més du document original et exposer les deux feuilles au rayonne- ment, soit à travers le verso de   1'original ,   soit à travers le verso de la feuille de reproduction.

   Ces variantes sont bien connues   et décrites   dans de nombreux   notamment   au brevet des Etats-Unis d'Amérique n    2.663.657.   



     L'exposition   du   produit   thormographique peut être obtenue par réflexion simple, comme décrit c-dessus, ou par le procédé 
 EMI13.3 
 dit nbi.-eflexn. Dans ce procédé, on dispose d-lun support dlexpo-   sition   très   perméable   à l'énergie rayonnée sous forme de radiations Infrarouges. Ce support est avantageusementrelativement mince, de sorte que la   chaleur   produite dans les caractères   imprimés   du   do-   
 EMI13.4 
 cusent original peuvent être transmis à la couche thermosensible à travers la   feuille   de reproduction, a ce qui produit   un     change-   
 EMI13.5 
 de couleur correspondant aux caractères imprimés.,sa,.Is retourneaent de lainage.

   Le papier utilisé peut être un papier ordinaire ren- du nor.en4anénenb tra,s,,.r.ent pour permettre l'exposition à iras vers lui. La substance rendant le papier   transparent peut   être 
 EMI13.6 
 ±1i#>née après 1 exposition de manière à ce que le papier de sup- port   soit   finalement opaque. Ce traitement rendant un papier momentanément   est     bien   connu. 



   On a aussi trouvé que   Inapplication   de la couche thermosen- 

 <Desc/Clms Page number 14> 

 
 EMI14.1 
 ,;""",-..,.....,,.. - -- .. ".....'-.......- i.&le' surYe 'support peut ne pas $tre faite-. de manière régulière '' ''7 ' "'.' ..ma:is' u 1 cm peut appliquer la couche thermosensibla non ùniformônent '1 # . :: :' suivant un dessin régulier, par exemple formant des lignes ou des pointa. De telles couches sont utiles dans certains cas particuliers, notamment dans les arts graphiques. 



   Dans ce qui précède, on 4 considéré uniquement une lampe infrarouge comme source de rayonnement, mais d'autres sources d'énergie rayonnée sont également utilisables. Il est avantageux que la source de radiations soit choisie de manière à ce que les rayonnements émis soient fortement absorbés par les caractères ou autres tracés   imprimés   à reproduire. Ces caractères absorbent 1'énergie rayonnée et   la.   transforment en chaleur qui est   transmise   à la couche thermosensilble. 



   On peut utiliser des corps incandescents comma source d'énergie   rayonnante,   puisque les objets   incandescents   émettent un rayonnement 
 EMI14.2 
 qui est g-Snéralenant riche en rayonnements absorbés par la plupart des matières formant les lettres imprimées usuelles. Si l'énergie rayonnée 
 EMI14.3 
 n'est pas transmise par a support portant la =>==,1=Là thermosensible, le   document   reproduit doit laisser passer ces radiations de manière à ce que l'exposition puisse être faite à travers la face postérieure du document portantles caractères imprimés. 



   Les exemples suivants illustrent l'invention. 
 EMI14.4 
 



  -ME"13 1 On prépare un produit ßer,oraphiçue en dépossnt sur un support en papier une composition contenant de la gélatine et du perchlorate de 3'-8tâ;I-7-sët.ax;-4''--beuo2pyxiâ.otbiacar'ocyayaïne. On plaça un   document   portant des   impressions   au contact de la face non enduite du papier. On expose le tout au rayonnement comprenant de l'infrarouge émis par une   lampe     infrarouge,   et on obtient   une     répliqua.   du document original, portant le   René   texte imprimé. 
 EMI14.5 
 



  3Jl2L± 2 : On obtient des rés 1%a=s analogues à cexax 3e l'exemple ' en utilisant les composés suivants : 1 à 10, 16 à 20, 23 et 24 à 31 de la liste indiquée ci-dessus. 
 EMI14.6 
 



  .E:o#!'1E 3 : On applique sur une feuille d' alut:iniur:1 une composition formée de gélatine et du composé n    13,   et on écrit avec une pointa chauffante au verso du papier. On   obtient   une image dans   les   zones chauffées.



   <Desc / Clms Page number 1>
 



  New products for thermography.,

 <Desc / Clms Page number 2>

   @ The present invention relates to products and
 EMI2.1
 positions er :: oôr.-ïçue: -: Dyes 1-a = are frequently used in thersographic reproduction procedures.

   To do this, the products of eT'2'register are often impregnated: e: w: t tne: -l: ogra1 = hiqu.e with dyes which change color by heating. The heat producing the turn
 EMI2.2
 can be supplied p a heating style C = 4: r -.:- G .:

  .iv by direct contact ,. or by an exhibition. to radiation of high calorific energy, exposure which is modulated so as to form
 EMI2.3
 a latent ealorifiquej by exposure in contact with a document to be reproduced, the various areas of which absorb and reflect
 EMI2.4
 the calorific radiance differs.

   L 1- = latent air ..- if forced produces a visible image by modification of the color-
 EMI2.5
 their colox-mt, saz-s deterioration of the original document .. 'A suitable radiation soxzr- This method of reproduction t.'ler :: igra- plique is the laz> e yarns of tungsten which bet a radiation rich in infrared and visible light. The thermographic process is particularly suitable. "Well for reproduction of originals having 1-irfra.-o-aged absorbent areas. Some of the known thermographic products are only insensitive to visible radiation and therefore require prolonged exposures to obtain acceptable copies.

   It is obvious that these products have only Usual uses and that, in certain cases, they present no practical interest *
 EMI2.6
 The objects of the invention are new the = - == 1ographical products characterized in that they cG: t? eren, co.:. e thermosensitive compound a compound corresponding to one of the following two formulas-.
 EMI2.7
 



  in which:'..'     @
 EMI2.8
 R1 can have one of the meanings s-: xi: ranss: - ¯ a) -a methin bond - terminated by a -hét6ro- cyclicue ring, of the type contained in the cyar.ue dyes, px exelsple one of the nuclei described in - 1- * work by Hees and Jases "The Theo of the Photography Processtt., 2-IacSillan ed., 3rd ed. 18 232a - the house méthJ-n po ,, ivan i ', - be substituted or not. And being ., by '].) example ime bond -CE =, -C <Ffl3> 1> g = ¯g -CH = C L.3- -

 <Desc / Clms Page number 3>

 
 EMI3.1
 etc i * ** ** * *** '/ bu an radical = xw1ià = zcvi-µ-le, such as a radical of formula,.



  -CH =, ^. N βF33-C6â, 83 denoting a hydrogen atom or a radical - '' -
 EMI3.2
 alkyl or
 EMI3.3
 c) a styryl radical, optionally substituted for example .. a radical of -C = C-C6 -, R 2 denotes a --tome of hydrosene, a croups alkyl, aryl or a groups = w1 :: s, o ta Wen t d4-a2: coylaraino, me! that iijê = hy.1a => o; -h lieut, have one of the following sgn2c os ¯. - ic> - a) a bond # éÏhixÉl = # 1 # created by a heterogeneous ccyau = ocycîique in type ccnterL in the colors.'s .. = oc; ¯î.G, described for example ¯ - ique ... ... r-on .às where-v = ace ¯recité, the bond nethiÔ7 = 1. = nt atre Lon 50E5sziàêe
 EMI3.4
 or substituted; or
 EMI3.5
 b) an optionally substituted allylidëca radical, and a cyanoallylidè1 radical: .e, an alkylsrboxyallylidee or ç3coylsuL oy? alïy'¯.idëne radical;
 EMI3.6
 'Little designate:

   
 EMI3.7
 a) an a1co radical; (! - e x3 'z avé1:;. t.; ", s"' me! l't de.1Ul b. hui-: carbon atoms, such as a radical = ézhà- 1e, proxyl, ethyl, cutyl, etc., this radical possibly being substituted, being for example an iai = cal sulfc- vlCGflG-9 such as the radical - (. 'SJ3, an aryla1cDyl5 radical, for exampleTBβJle a bE radical. "1 ".c.jr '! By or a salt for example - (cE) ¯-J-1, Y denoting a salt of pyrr¯w: .¯u. substituted or not S1.1us't: l.tu.e ;. z, an acyl radical, for example -C (C} -: a4 where 'G3 an alkyl radical z3. 5 having one to eight carbon atoms or an aryl radical, for example a: methyl radical, 67Zby'te , propyl, bu; .y: .e, phenyl, aap; re, etc, cs c) an aryl radical éV (1: .. e2.1c :::

  ent substituted such as phenyl, naphthyl, s zo-y3e, etc. Z represents the atoms necessary to complete a ring - heteroc, vc! 4-, C-, a 2 five or six membered ring, this ring containing

 <Desc / Clms Page number 4>

 
 EMI4.1
 at the moiré another atom, Clu "an otoxe of. Carbo: .e,: .el ÇU'1.ln .atome doÀ7;! mc" of sulfur of s, rlén1t.:. :: 1 or of'ao4e, This nucleus tt: .. "'1t" by oXeYl, L: pyridinc nucleus ##### uir.ol1e "ec;

   X .rercsc.:. E an anion, such QUI ax: ica cfào * 1 = -e, broure, o- de "? Orch1orte ,, sU :: ta, = oc; a. :: e ,, sr-to : .è.e sw..3.'onate ,, i: 3E. '' 47; jJ.Sl. '. 1:. "rf3, viiJ F.:.tii;0 09.OIF.' 8, e Cj The CO05'S ê6ir.ls 6set us = 10 of properties which make them usable in various processes of obtaining wa, es.Er discolored by the heat1 they are: , = ..- e; r, 3 ut4oÀisies in ,, re wa; r, ::. e., this ç # 1 is the subject of this /
 EMI4.2
 patent application.

   We can prepare the compounds used following
 EMI4.3
 the invent1on coe == e describes it of = ---. of Belgian Patent No. 78 51t6, filed August 29, 1969 in the name of the Applicant. The compounds defined above are ch1 = ue altered when subjected to bzz c. "'1auf.f': lge,;. ar example to the heat provided by red radiations. ':' I; t: 2'8 cé # é = a = 1e, this L "i''c, 'rc":' v ... 'OI3 is u ... "' :. cut of the ::: ollcule, do 1 ,: .. '. C, ::. 8. ".. E.' precise depends on the precise compound used.

   This 1tÉcx # isr: e ..-....-. 1 '... a-: J, ..... c na- niere 1 "' ..... 1 ...." ,, ! <'> nr> a .. ""' ''.) at SU'h '' '' '' ''. a. "'' '' '1' '" on a specific example:. i --.- '"C e
 EMI4.4
 
 EMI4.5
 The èLc.Qh .. -; O: l x- actio; Ga- '1-at: .i'.: Téffa- i?; - ft- &;;. Te ::. Ue-:? R- CO.P htL-'Y "" l'q "C c. 'c la .. "of O" "from 4.: e to o" "' -" '7 "ion 14q.D + and%, - ne base V l1oo4o .l..¯c.; .... ;.;> ¯4 .., éC S $ Y'c ': - a. ^ ..: sL' - "'-' \,; -" --- ...... "'... ..L ... e ose colotc which had = e ± rcte è4V; 1tage.Cest iette. Base cJlon-nta çr 'is "ilis6e 1> ohte = ticn d'iges.Les'."'; - 1 "" 5! '--- ", -"' - -o .. ,, ".... s the cO" "" "The C. ' -. ^ w ¯-1, .., o:, "" 'vc "",: - re,.

   Pro "- éZ * .Orce-- dive-zes reacl - 'ons i rue' 1 'ïSt" or la .a .. o wi r..t ..1 - ¯.- "! A -01, , - tso OR l r6c: o. cOuer oina qse le # da ap- = ..: ': nt C:;': 2.d 0: 1 and <.i te pr 1.:-, acid dc- ::: a., ièc; cue e; 3. du. ;;:;: 0- .a soi '# Sé =' n = ± 7, -às ne ",: 1. "" '- "..... 1 ..' - ':) zz ç- v ...: ..: .....:;,." ,, - C, 7, lZe C-, Za - 4d = 'L' coo- "" GSi.

   J, 'l: ad <' IZ¯cCw L't'iZ''3C '... r' '' '' '' '' '' e a4CWi des frh: ;; :: e :: ts,; .t: 'Oc: uits WW.4r4' from Va.rY'v'1.J4S ièes:

 <Desc / Clms Page number 5>

 
 EMI5.1
 eg exe2e, Ia? d; .e is an effective re4.-iculation-ët--
 EMI5.2
 a dye mordant free radicals and cations are
 EMI5.3
 polymerization initiators. "".; According to various advantageous sodas of ease of implementation of 1 - ,: Ln- veion, has atiise compounds theraosensitive ca: fa es to the de-
 EMI5.4
 general finish given above and corresponding more gone ---
 EMI5.5
 to one of the following formulas - '¯¯, ¯, ¯'.] j
 EMI5.6
 ¯ ---- r-GgTC-s-h - a-s = GE ---'- E3 g n-1 - 1.



  2 .. OR ¯. - -I- = - i = - '; ¯ .fl "rut oy" l ', ¯' - Î '/ 1. R-l ± ¯, ¯, OR E. ¯ D. - -; . ''.: R2 ,,. -qÔi] =? = 1. fr ¯, 7% / "'é ¯-' ¯ ¯ ¯ 'Î - C) = c3-CH =? = C- # L = L - G ô., ¯ ¯ ¯ -! - Sl ¯ n ', 1 1 ... 1 - "X. ¯ ',? :. '"= -, .- ..?, - = E2.", "- <;.'" Î ('' i "" ..; .- r'X - -. ¯ ', lli "Ù" Ô /;. ,, - Q? / ,, -Q? - ,,, -: -: D) .C ^ 'it-s- = s T r tr â Y iT:' 11. -,; -] / .. g-1 .. '-. -s '' ¯ - "",. ¯. -, ...



  -: - / '' ... L.; - ¯ "'ÎÎ" j. "V 1" / 1 ± "$ -; 2 OR 2É '^ ¯ -q2 1! -' - ¯ f" s bzz 2 ¯ ¯ ¯ µ, -Q2¯ nY) - RO-N - SE = CH: --C == LL = 5 = C ## & = 0 or. g-1 m

 <Desc / Clms Page number 6>

 
 EMI6.1
 
 EMI6.2
 5> "In these ornules; the 'symbols have the following meanings: ¯ t,. -. QI,' Q2) 'Q3, e Q9 each represent the nonmetallic atoms' needed to complete a nucleus A sensitizer or desensitizer comprising a heterocycle with five or six atoms, of which at the corners an atom other than a carbon atom, such as:. atone of oxygen, sulfur, selenium or azo, that is to say a
 EMI6.3
 core of one of * types used in the preparation of dyes
 EMI6.4
 - cyarii.ne? such as one of the following typical cores:

   the nuclei of. thiazole fani3 "e, for example royal thiazole, 4-methylthia-" zole, 3-ethylethiazoles 4-phb..y1thiazole, 5 - :: 1ethylthiazoJ..e, 5-phenyl-.



  ¯¯ thiazole, 4,5-din: ethylthiazole, 1: -, 5-diphe: lylthiazole, 4- (2-thienyl) -:. thiazole, benzothiazole, 4-chlorobenzothiasolej 4- or 5-nitroberso-5 tMazole, 5'-cJ> .. lorobenzothiazole, 6-croro erlzo - :::: -. d.ê.zo1.e, 7-chloro-. ' benzoNùiazole, 4-nétlflylbenzothiazJle, 5-éthyl.bB: lZot: rlazole, 6-methylbenzothiazo.e 3 Er.4r ooertzo .aZOIe y i-bxraàbenza L:.; a.zole, ¯6- bronobenzothlazole, 5- chloro-6-nitrobenzot; hiazole, 4-phenylbenzo- - - thiazole, --é, oxyberzzo4biazo.se, $ -wéboxuenzo = .àaza3e, 6-methoxy-)> benotiniazole, 5'-iodobenzothiazole, 6-îoiôDenzotàîazole> 4- ethoxy- .é benzo 4 '..' 3 azo '' ej '5 -é - :::: J.0) :; Tbe'2; ot; -iaz01 ... e;),' -. T x ay 4 oiē'ïzo V âsazo.e 5,6- d: é ¯oxyberzo '^ .. azal, 5,6-zethylene (ioxybenothiazo? e, 5' -? ydroxy- -benzothiazole, 6-hydroX "i ' benzothiazole, a-naphthot1 - .. iazole, p-naphtho- '-thiazole, f? .1 ......,. l $ -cL:

  oa..s3¯napoLziazo? e '"' ...... f? hL .1.hi." 1 8 "o .. '."' t-.; .. ', 7 "t", t P-naphthothiazole S-setho-x-naphthotasole 7-r4thoxy-c: -naphthothiaole, ':' - vé4bcx, ynaTaphc: o -; 'a6', =, $ - û-: iazo? E, nitro- napboz.aLo3es, etc. ; the rings of (x # i7e of 3.ja: azole, for example the rings 4-methylcxazole 4-r tro-oxazole, 5 -;:;. eth'loxazole: 1 4-phenyioxazole) 4,5- diphenyloxazole, 4-eth-yloxazole, 4) 5 - diJ ": 1ethyl.-} oxazole, j-pbény.oxazoes benzoxazole, 5-chlorabenzoxazole, 5-méthy-" tsenzoxazoie, 5-phenylbe (oxazole) Ç- or 6 -5 ± trmDenzoxazole, 5-chlo, - .. ro-6-nîtrflDe; zo> azole, 6- = étlÉyînenzoxazo'e> s $, S-di ê hylbenzoxazo'i e 5.



  3-s6-diéL: y.benzo: azole, 5-methoxybenzoxazole, 5-t: c.o7-Yben2oxazole, 6 tëboxßoe: 2oxazoie 5-hydroxybenzoxazole, 6 - ydâohybenzo; zcle,, oe-na> htoxazalg, p- naphthoxazole, the various nitro naphthoxazoles> etc.;. the nuclei of the selE?: azole fasille, for example the 4 -!: 1ethylselenazole) 4 -; - li rings. troseleI ".a.zole, 4-phenylselenazole, benzo-: selenazole, 5-c :: ù.o :: - obenzoselenazole) 5-methoxybenzo5 elenazo1e;, -hYdIoXYbenzoslénazole, 5- or 6-ritrcb? nzo <elénazole chloro- z

 <Desc / Clms Page number 7>

 
 EMI7.1
 fi-nitrobenzosé3énazaiei 'éir, y3 = ôcenzos2? enazQîe, ocaapßosé3én--]; li = q¯. âoïe, I3-naphthoselénazol, the various nitro naphthoseîéna'zo2esß etc, r> - - :: - the nuclei binds the fault of the 1; hiazolÛle, 'for example the nuclei¯ thJ.azo3ine, -et.' '., -, 1 iazaline, etc;

   the manila ncysnxes of pyridine, for example the rings. 2-pyridine, S-ne: hy2-2-çyrid.iae .. ¯ ¯ 4-pyridine, 3 - thyl¯4 y '=' iain the various i-tra-p-, rièi: .es, etc; ' - ', the nuclei of the cuincleine and 2' families; soçs ::. oîQi..ex for - examples the 2-quinoline rings, 3-mejy1-2-qu ± noléhne, ¯ $ - éhy1- 2- quinoline-, S-chlora-2-çu.nolée, 6 i: ro-2-çuJ.no3iae, 8-chloro- "2-quinoline, 6-xetoxy 2-çzircïéī ^ ¯e, 8-éo uinoline, Ey - Q 3roxy-2-ç :: ixozein, 4-quinoline, 5-.:.éLo--çuinoline, 6-nî = rc - 4- quinoline, 7-nethyî-4 - çnirolé> e, ô-chio = o-4 - quiwlolein, 1-isoquinoline, 6 xißro-'F-iso; uo? ein, 3, .- 3i; y-a -: - isacinoinei: ga 3-iso- - quinoline, etc; kernels.!: 3,3-4iaîcoy? i: .dcla, por-: ant avata # geusesis a suostiTxant nitro os., a:

   o, 1; e: B f ;;. ua the rings 3,3-di-zethyl-5 or 6-niz = indoiéirn, 3 = 3-di; G-t '. ^ iyl - on 6-cyanoindole! : ir.e, etc; nuclei of the i'¯d22ate family, for example the nuclei, imidazole, 1-alcoyli = iàezole, r-aiçoy? - # peaylir..ic.azole, 1-alcoyl-4,5-diEétl! yli! aida = ole, aaz¯ .. ^. ¯3azole, 1-alcoylbenzi ::. idazole, 1-a: co; l -: it = oenûiidazo '? e, -: yï-1a6.ic' -. îorGbenxiidazo3e, 1 -alkyl-x-aa? htidazoia, iy? ¯ï¯na, 4i: .da.o2e, 1-alcoyl-5-ce- T.hoxy-o # naphtalisidaz & le, the nucleus of the iidaso4t5'- 37 * 'quinoxaline, by ± -.xc, i = e les.: Gy-u.'. X I- # lcc'i = i3 == of4, jfflc # ± -oxaii = e such cse -ô-ézhylinida = of4,5> flq'aincxaline, 5-chlo = o-1-ê = ± rlir = Ldazo- L y5-Jçsincxa3i! e, e: .c, 1-Q.lc:::y li - :: d. dazoL 4, 5-Êl quinoxìr..o, .p <:: r 'example 1-al $ yliniéao ± 4, p flq'iGox = lî = o, 6- = h'oro-1 - <- lylimidazo- f4 ,> flçuincx = l1 # e, 8'LO,;

  -a = iioi # zoS4, pflquinoxàine, = r example '-gény îî: 3azaL, --ç''oz << iaes 6 = Elo = o-1-pEé = zriinid == o- L 1,% -guinaxaliae, e ta the nuclei., --àia. '. coy3--3 Lyrrol a, .î - =? 7 pyridise, for example .î, 3ic.étî-s.¯ F'rraîc, Jp: fridine, 3.3 - d: .é'L: ß 1 - ,; ß;%. T3'OiGL 2-, b% p; 'râa, summer; the ::: oya-a 'thia.zcloL4,5-ÈÏ-
 EMI7.2
 quinoline, etc,
 EMI7.3
 R3 xep = this gnoup.,, ... 1. - represents group -coy.e éventnellesen '. uas' .. i'.éj avan J; as6use:; en't a lower alkyl group, c ^ .y:. ::::. a1; ra a% C = e3 of carbon, for example a methyl group, et: yîa, propyl, isopropyl, cu-tyl, hexyl, cyclohexyl, decyl, dadÉCyîe% e1; c, a group 1; ydroxyc.lcoyl, for example p-hya-ozyrê * yie, L3 / ny> oxàJ.aty? e, etc, an alkoxya.lcoyl group, p <-X "example # melTh.oxyethyl tal # buto.xy # ÙàYle, 'eta;

   a group ce. = SOcorie.- - ¯ example J3-c.arbox;) 'le, kà-czflooxybutyàe, e t; , an alaa-j group, eg - ############

 <Desc / Clms Page number 8>

 
 EMI8.1
 pie m6-t-oxy, e.za3xy etc,, -a group ... t.: ...:: -: 5 .-. '. to.â:; by ... ",, ..-.... 1 '" -' 's ..' .. 'C3 ±: y s.é-.fi. s.:.':7,.'s3:.=. .2 g L C. y, 'c: - =, t;.::' I "â. ':' C;. :::. ¯ '' .. Ci; f â .B by O: .. ............ "" .....-: 3..t ....... .....- û.'s: EI? ¯: r. ' ''. ', r ".... w .... ..â ..' n? p2.r L3 '.,. ::. ..: 'fl -, = 5-. tlaox3rcai = -> Lé = 1 = ;. 1 <, -; 1-àt ± = ox3rca ± Joylbutj-1 *, c-tc.

   C ..- t ;. <"; y ': ..: p7;' a "EZ- 'C; r'.e ?. eg ::?: e .., i. <iy6 p1: é ..: f ;;: yle, otr, 3. ; :: j ::;, i: :: ". :::; 1; not: 'é ..' .. C .1 # y # &2-pop;: yle, 2-jaté # 3.le , y tJ::. '. c'n. in:; - =;:; ".;' a a == il ± ¯ xà> CL'j..B3 i. ^ 7:,. ' tc1.y2e, -? ::. tyle, é ::. o ""? ::::: r2 :) chlo = <: # 3 = 5 # 1.'lc etc. ; bzz¯ 1 '$ â. 'eSc.:,. eS a' â.O.A '.. 5: ^ v' w ':. rt,.? .... j ..:. ¯t 'M .:.,' '::: s = t' ..

   S Ss. ¯ L'sr r30 '.: "# & reprqsërLt & the atoms .ncs L-- = .. cessa.ires; poTir' il .: r-e²'- sc :: ¯ the atones 4"; "" - ":: ;;:", ... ¯ --.....;: ... ;;: \, .. <;;; $ ;;. ", -) .J-) complete ' u a1Jyau heterocyclic with five or s> = W.4 s CVwaVÂ ^ KsirV followed 'r' 1% example i "Un j 'MÇ1 è ..' i: lzote, da sv-: re..s. ± 6¯- {. ,, ",, ;; 'o'Y" "VC- ,,,,,, 3 ^ 1 C'" '' 'l' '' '' 'n'f -u- "' '' ' - '' '2 - "' -" "" '- c "': '::':" '¯-0 -: - I .'- "" "Z;'" e ",.", " , "'P" I, 1% on oxygen, such,. \. 4. "--i. noya-n 2-P = a..cw¯ --o ::: (p3.r example L t.:',.-" i.:y 3.-G "" a's ?. Tr ....;: "'tÂâ.f'. 'W"'. 1: L ':' ... "'"' rt c, .. ". Û.r:. -T, i.



  't¯2-2: .. "ov:.:. 2: o? y'! i- i-: Cyī? - .Oz¯: -js: y etc.); g noy .'fJâi '. 82'.o.¯O:. ± -...... SÂ '.. ".." r .. .4 y -: CI "". F ..-! 1 :.' f = 'Cf. .. L ... O¯. #. 3-ethyl-5'- tE) -isoxazo! or.e2'etc); 2L7. S: Oya; x O: i: .. û: VS.' (; r examples 1-alkyl- 2, 34ihyWàn-> j-2-o> ii # to + le. eta.)> rxn -..... "w. :: (. 4 ¯.vs; av; jr ... such tjLi. 1, '... radical acids barbituric or acid -; ::.:. Oa: - ::' i.t1.:.iQ .ue carrying eventual = ent àos substitus-nts 4a'.Yoi.L4W..i position. 1 (1 mi4Lriy 1-propy2-, 1-hepy?, etc.) or had positions 1 and 3 ('y 3 -.;: ét: yl- #. 1,3-d.ethyl-3? si-cip = ePy.-y .s3-üsopro = yl x = - :: iyc.o: e: f.-3 13 -di (aethoxycthyl) -, etc. or substituents û f. '..

   L'1 position, 3.- P ÎIGIi Yl -s 1 -? - chlorc> hey # ylL, 1-p-ét2: oxycar '!: Lo ::: tlpényl-, etc.)' Or in positions 1 and 3 ii, j-toiK-1e; yi-, 1 $ 3-di {pc: 10 = c: r.yl-, 1,3-di- (p-ethoxycarboy1penyZ-, etc.) or an alkyl substituent in posi- tion 1 and 'm substitca; t aryl in position 3 (1-ethyl3-3-p: nyl-s 1-n Y.epty3-3 hû: yl-r etc.), such as a rhodanine ring (c' is to say a ring of 1 fa = ille des 2-tb-to - ?, 4-th4azolidinediones), such as a rhodanine ring, 3-alcoylrhoJanine, (3-ethyl-hodanine, 3-allylrho-danine, etc.), 3-carboxyalkylrhodanine (3- (2-carboxyethyl) rhodanine, 3- (4-carboxybLtyl) rhodanines etc.), r-suloulcoylr: aodanir.e, (3- (2-sul- tothy2, rhodaa: iz : es, 3- (3-sul2opropyl; rhodaHi. ^. es 3- (4-sulfobutyl) rho-danine, etc.), or 3-arylrho: anS.: e .. (- P; nyir: odan.ine , etc., etc.;

   such as a nucleus 2 (3-iaidazo, '12 -pYriàa: e or 2-.fu: -anone (3-cyano- -phny3 .- ('Ej-turanones etc.): such as a nucleus th = o.i'.én-3-o: xe-I, 1- dioxide (benzobthioghn 3 (2i: -one-lsl-diox.ide etc.); such as a nucleus ,, 7'âiOXO-b,? - àihy dra'-thiaZOio, r3f2-pYxiuidi: .e- (a? -d3.oxo-.



  3-IAYl- s? 3'3xo- $ iziazolo, 2-Pyrinidir: e etc.), such as a 2-thio-2,4-oxazolidinedione ring (i.e. a ring of the fa-

 <Desc / Clms Page number 9>

 
 EMI9.1
 ........... ui "e of 2-t: ûc-2'-r i3 =: .- Î-03.'az0¯''iU ': U' $: é. =: : ': f: 2-thia-2,3 - ox.- zo1iàOedione,, 3-C, 2-s: .Qéthy33-2-thio-2ir-oxazoLidineaione3 3- (4- sn: Ic, utyl) - 2-t'hsa-2, - oxazalitin edior.e 3- (3-carbo3rypropyl) -2-thic- ¯ 2t-oxazol3di.ed; tr. ^ ¯es etc.); a thianaphthenone ring (2- (211 ) -thiana. phtenone, etc.): salt that a nucleus 2-thio-2 5-th.îazo2dinedione that is to say of faaiile & s 2-thio-2, C3H-ï ') - thiazo? ec.iones) (3-ethyl- 2 = :. ho - t: azolîdinedîOn23 etc.); such as a 2,4-thiazolidir diona 2jt-t ring: .i.aza'¯idir.edi one 3-ethyl - 2 - tâ: .azolîdi .ediones 3-phe-¯ nyl-2,4-trazolidinedione, 3-α-ryhtyl -, - thzazolidinedione etc.);

   such as a tiazc3ici = none ring (4-thiazolidinone, 3-eth714-thiazodidinone, 3-phenyl-4-thiazolidliione, 3r.s-naphthyl-4-thiazolldin.one, etc.); such as 1 nuclea 2-iazolin-4-one (2-É thy? rercap to-2 thia-zolin-4-one, 2-alccylphenylanino-2-thiazolin-4-one, 2-diphenylamino-2-thiazolin -4-one, etc.); such as a 2-inino-4-oxazolidinoae nucleus (on) psEUdohydaitoi ^ 2) such as a 2s-iidazo? idinediane i (hydantoin) nucleus: 23-iiêazalscinedio: e, 3-ethyl-2, -s-- iidazolidi.ne- dio # e, 3-phés.yl-2,: - ir.idazo? idir.ed.one s 3-a-naphthy3-2 --iidazoi.- dinedione, 33-c ..> ûhyi-2-? idazo? idinedione 1-ethyl-3-phenyl- 2, "- 1: xidazo ' iài, eài = n #, 3-éü; = .- 2-x-naphthyl-2, - iidazo.idinedionei 1,3-ui;:

   enys-2, -, a.aiû.c'3ZOt? .cl ned: ion e etc.), such as a 2-thio-2,4-imiàazoliéinedione (or, 2-tlaioànydanto] ne) ring (2- thio-2j4-imidazolidinedione, s 3-et: y i-2-thio-2s-i: i dazo? idinedione, 3- (4-sulfobutyl) - 2-tliio-2,4-iidazolidi.edioiie, 3 - (2-carboXyethyl) -2-thio-2j4-inida- zolidinedione, 3-phenyl-2-thio-2,4-imidazoidinedione, -3-a-naphthyl- 2-thio-2, Y-iridazolidinedione, l, 3-Diethyl-2-thio-2,4-imidazolidine-diane,.-Et: yl-3-phenyl-2-thr o-2, Z: -iidazolidinedioney l-ethyl-3- rô.p.ayl-2 -thzo-2, -iidazolidirsedions 1,3-diphenyl-2-thio-2,4-zimiàazolidineàione, etc.); or such as a 2-imidazolin-5-one ring;

   (2-prohylmercapto-2-imidazolin-5-one, etc.); - n is a positive integer between 1 and 4; ; - n is one two or three .; ,. g 6 is 1 or 2; ¯ * j R6 and R each denote a cyano radical, an ester radical (ethoxycarbonY7 nethoxycarbonyl-, etc.), or alkyl-sul- ¯) rony1e (e: hylsuli "onyl-, ethyisu3iony ? -etc. 3; ---- - - .- - - # "" "" - L represents a methine chain of iormlxle # C = or.

   T "2, ¯ ¯ at a hydrogen atom, an alkyl radical having from 1 to 4 atoms
 EMI9.2
 te carbon or a. aryl group (phenyl, etc.)
 EMI9.3
 , "¯, - I. Î, ÉÉRtBÔÎ / nÉntlllÉltàecs. * .. - D, E, J, R2 and R4 independently denote atones. 1 ..... .. ¯¯ :: '' ..-. - -

 <Desc / Clms Page number 10>

 
 EMI10.1
 of hydrogen, acoyie groups, content av.nt.t; weusent from 1 to 4 carbon atoms), (methyl, eibyl, propyl, isopropyl, butyl, decyl, dodecyl, etc), or aryl groups (phenyl, tolyl, naphthyl, methoxyphenyl, ni-.ro-ah, 64yl, etc);

   X represents an anion, (chloride, bzo = re, iodide, perchlorate, tatrafluoroborate, thiocyanate, p-o2zè: es sulfoste, stêthyl #
 EMI10.2
 sulfate, etc),
 EMI10.3
 G rapreser¯The un r4dicl enilino cn Lrzle, (n ± é = y1 <, naphthyle., Diaiccylsinophenyle toîyle, oIorophênyï,> z = z = ojhé = yie ailinsvinyle,
 EMI10.4
 summer) ,
 EMI10.5
 = ep-é; ente raiix = 1 -1. =; j.Il # escy - represents a radics.1 #######., .. 4 .GÜ: ßt syEn '= t.'. 't1â '.0. ^ .. 23 of C L7Gae dt-ns la ebai ## 12: cy, 1 -.:- .. = n = iàic = 1 l's'. 'w: .a for =' .. Ie (C ') -.r ;? ens- (Cn; - -C,, eu L 2a *. # ioi = i to 7 2, such culun K * fa ¯ cri, zét = z- = ethyî- eneoxy,; rox3.liààneaxy, étl'.L & nedo. xy,> = é = y13; -ùhi # ézEoz3 ", etc; e - 2 nep = é-en2e aoi:

   a = aiic =? alkoyia. optionally substituted, - aya # t = v == t = ceuzi # i = I from one to four atoms of ca.rbcne, such as an nsthyl, ethyl, propyl, isopropyl, buty'-Ie, hexyl, cyclohexyl, decyl, d0C ''. EGjl $, a radical q7.i 'a censyl radical, a medical sulfoalkyl, xar example 6-sulfoëthyle, # sulfo'butyle, # sulfopro'oyie, or an acyl radical, for example a radical of formula -C (û) -3 where Ru for example a ⯠curz: ézh5> ¯e, 2myle, napn ß le, propyl, be: ¯ :, etc.



  In the preceding formulas, Q2 preferably represents the ator-.es necessary for a pyridine or quinoline nucleus, D, ez J are preferably zldio = x aryl.



  Typical of light-discolored dyes and internedisires for their preparation are the following compounds: 1. 3-ezhyl-1'-methozyoxa-2'-pyridoc == bacyanine perchlorate 2.tetraßluorobcrae -ethox3r-3-ethy? qza = 21 = ¯pùridqcaTDocyznîne iodide -le 3'-ézhyl-1-néthoxy-2-py = idoihî = cy ine 4. técrdluo = obo = ato àe 1-éihoxyr-3'-ethyl- 2-pyridcthiacy == 1nB 1-Benzyloxy-3'-ethyl-2-nyni-ioil-iacyaz * iodide 6.3'-ethyl-1-xelioxy-2-py indide = ido = hîac == bocyznine 7 .. zÉ:, ß aï? i-ethoxy-3 * -ezhyl-2-sy ucrroborate = iio = hiacarbocyanine 8. bydrcXy.de de anhyàro-3 '- * éthyl-1- (3-sulTo ropoxy) -2-Qyràào = hia-earcocysnine perchlorate de 1-T: en2yloxy # 3 '# eti! Yi # 2 # pyridothi.aoar'bocyanne in, 3'-etl-1-aého-2-pyridothiadicarT perchlorate: ocyanine ¯¯¯¯ 1t <picrate of'! '# metho2y-1,3! 3-trisë '):

  hylindo-2 '# pyridocarbocysnine

 <Desc / Clms Page number 11>

 
 EMI11.1
 12. ae 3T-e perchlorate; i-eyuor, -ç? 7 - nenzo-c pyrzaozacaruocyanui 13.! -ethox-, 3'-ethyl tetrafluoroborate, 3'-ethyl- ° 'y' benza-2-pyrido- - -. ": thiacarbocyanine 14. -: etrafluoro'bora'te of .l'-ezhoxy-3-ezhyloxa-2'-czbocyenîne 5 15. tetrafluoroborate de 1 '-é; hoxy-3-é; 1 hia-2'-cyani .ne 16. # é = IIt02'ObOr a: e of T-ethoxy-3-ethyl? hia-2'-csrbooyanine 1 ?.: éi.Z '<zW.OrCJOrôwe de?' - c :. '.. Cx; f - .. z'yv: 2â-2 '-.'. WC r: / OCjI '13 âI6:. 2CL: .dnZe- G6? -. '^ "W¯LSYßr -'-.' E. .j'i - #. i - ". On.ir.COir.

   O: 'û "bOCy7.33g': 9. 3'-ethyl-j-cXY-4-py perchlorate = idolacyine 2J. 'R'" ¯ 2 C. '. J. CrfiW.' of 3'- ± '.r'i-' c: # ¯: O, fT-Jy = 1tlQ i. '. ". lâCnT'ûOCy cwj.:uB 21. memr = ii; o = oôo> a = e de? '- é: = o.ay-3-éz = v'j- = s u-oenze G': = bocyanine 22. po: èè-31: ot6 de 2 - w ... ¯inovi .. zyi -? - xetozy:; f diui; 23. aerérhlo = ate de i-é i, i-l '- :. é.: - r- n j? = Oer.zo; 4w .'- c-. âocrrins 2L. dibroin-ire de '' -tz, ', rl2ci ..'. OX ', / Dl5Dj2: .. ^ înil: IL1 25. 3bro:., = re de ï = 1' - = ixéß: yiue.iu-3lazs # yridir'¯ .....



  26. d .. '¯D20. 28 e 'ii: "ßc =: G:" vïs: cr.30Xj% 335-2 wéT.;% 1..72ciiti.



  27. dibrcsnire de i, i'-érawé; "vlë: e - ,.; oxyhis (4 - :. ct :: ylpyridiniua) 28. d-bro = -tre of 1,1r-tet = aétsr.6ioxYDispy = idinium 29. dibro = u.re de? 3? '- pen-sét:;, r.èna ^ .iaryioispyri4iaium 3C. 1-acetoxy-2- (4-di = iêtBylasinostyryl) pyri <iijiium 31. perchlorate 1 enzayßcxy-2 -; # - âi.ét: ^ ,, vla.:.inosvyryl)pyri in¯u 32, # ..., .. ^ .. 8 's. ": é.: y --e- S s- é .t.GT-2- (ij - yr¯dyi.déne j W <.y <i4én 2-thiobhi ruriçue 33.:, - éi'i-l - (? - aëhox3--2 ( ? :: j-Yyri.; l3dènejét? ylidè: ¯% ho, .e 34. acid? 3-âiél - (? - ec, f-2 ('13 -pyriôyy..idànaëßh; 3idén ba - bi- .uric 35. t3, 3-3ioyaaaaliy2idër.e - i-wé;.: oxy- ?, 2-drâropyridins 36. 2 -% ('- xét.'. flx-2 (? E) y rid;,: ièsre -E iylidènbenzor #} .- 'opEëna- 3 (2ù) -one-1,1% -àîoxyÀe 37. 3-caa.' o-- r (3-ë: 'aox, Y-2 (? E; - p, r iây3¯3ëne j é ts: yiïdèn-t é:, 'ī 2 (53) - u = custard apple.



  The dyes defined c:, --- above, plus pa = zicnliêrez those which correspond to one of the formulas A to H, can siù * x1i = to obtain thermographic copies of documents. As has been explained, these compounds break down without 3 'heat ac iax and lose their
 EMI11.2
 initial color: generally they fade, which allows
 EMI11.3
 Use them as t1 products: ermosensièJ.es. Compounds forcing the photosensiole part of the leaf
 EMI11.4
 The reproduction can be deposited in layer on a support or move to impregnate this support.

   A support is used more particularly

 <Desc / Clms Page number 12>

 
 EMI12.1
 . "<'*% *' 1" '<' t! g: z "'é" ..... -1 ....... ttillsar' 'having low thermal conductivity 06nerueAl8nt, n hair use plain paper as a backing for a composition and paper., pot before being transparenty trluc1d. or opaque. It is frequently desirable to use a medium which transmits the expoaitian 4.:-d:.nt rauations particularly to the original reproduced as opaque for 041148 - here; at least one of the sheets (original or reproduction sheet) must be transparent * to used radiation.



  It .. '1 advantageous street the support uti11;., Aotacexnt on paper or * n other floral product, not begin pu 1 oarboaisar before) 25 * C
 EMI12.2
 about*
 EMI12.3
 For p-psrs: the product * twerograpkxçuss according to the invention, a layer of ooloraat ther :: i08naible is generally deposited on an opaque or transparent support. J.'p: as, obA [; Q, we place the reproductioa leaf in contact with an orisino: o containing lines, for example nn tsxa tnpé la machina à and we exposed 14 everything to rad1a- tio * = a 1ni "ro ougoa ..

   Ias pln "^^ es of the docutMnt ri reproduce which absorb a lot tra. Infrared rays, rsa: orsaen: these r & .yor.n.men ex heat, which oai t: s: .siss à lys.: E :: = îîa do copy, which produces rtpidex-Mt a ciànùexext ào aoaloa =: 10: .. 11,140th pla-os of 1 * excavation of = * px * oiàctio = which its: en = ag = 1 of the P :: '; 1 '' 'U $ ab; o = bant the heat of the document to be reproduced. The places of the copy sheet which are not in rc $ <. Rd of the dite pl. Du doo # ren = y .... ^ . ::::.;. t oa: r'1cson les:.-... iiutl.0: '4a 1ni'ra: rot; ès, so that it is produced p .: of xodification da color.



  If we deairw it, one can w.cpCr.:er the aaxpoada therxosea-

 <Desc / Clms Page number 13>

 
 EMI13.1
 , the s1hles in a binder and. deposit on the support a layer of -3a: '-' a ;; #: composition thus forsée..Parai the appropriate binders, one can quote 1-ethyl-cellulose., l, alk6or-polyvL-iyliqile, la, gelatin, co2lo-V dion, 1 eacetal-polyvinyl, cellulose esters, esters? hydrolyzed cellulosics, etc. When a collaldal binder is used, the contrast of the copies obtained can be varied by adjusting the amount of binder.

   This is well known to specialists. Various aesthetic effects can be achieved by adding pigments or inert dyes to colloidal dispersions, although there is generally no advantage in doing so. In some cases, an apparent increase in contrast is observed by introducing a coloring pigment into the colloidal binder.



   The source of infrared radiation may be arranged so that the back side of the original document receives the radiation, although in such cases it may be expedient that an insulating surface be applied against the back side of the original to localize. ser and intensify the heat received by this original. We can
 EMI13.2
 also following another di: sDos - 4 'ion, t, place the heat-sensitive layer of the reproduction sheet against the printed characters of the original document and expose both sheets to radiation, either through the reverse side of the The original or across the reverse side of the reproduction sheet.

   These variants are well known and described in many cases, in particular in United States Patent No. 2,663,657.



     Exposure of the thormographic product can be obtained by simple reflection, as described above, or by the method
 EMI13.3
 says nbi.-eflexn. In this process, a very permeable exposure support to the energy radiated in the form of infrared radiation is available. This support is advantageously relatively thin, so that the heat produced in the printed characters of the do-
 EMI13.4
 original cusent can be transmitted to the heat-sensitive layer through the reproduction sheet, resulting in a change
 EMI13.5
 of color corresponding to the printed characters., sa, .Is returned woolen.

   The paper used may be plain paper rendered nor.en4anénenb tra, s ,,. R.ent to allow exposure to it. The substance that makes the paper transparent may be
 EMI13.6
 ± 1i #> born after 1 exposure so that the support paper is finally opaque. This treatment making a paper momentarily is well known.



   It has also been found that the inapplication of the thermosed layer

 <Desc / Clms Page number 14>

 
 EMI14.1
 ,; "" ", - .., ..... ,, .. - - .." .....'-.......- i. & the 'surYe' support may not $ be made-. on a regular basis' '' '7' "'.' ..ma: is' 1 cm can apply the non-uniform heat-sensitive layer '1 #. :::' in a regular pattern, for example forming lines or dots. Such layers are useful in certain special cases, especially in graphic arts.



   In the above, only an infrared lamp is considered as the radiation source, but other sources of radiated energy are also usable. It is advantageous for the source of radiation to be chosen so that the radiation emitted is strongly absorbed by the characters or other printed traces to be reproduced. These characters absorb the radiated energy and the. transform into heat which is transmitted to the thermosensitive layer.



   Incandescent objects can be used as a source of radiant energy, since incandescent objects emit radiation.
 EMI14.2
 which is g-Seralenant rich in radiations absorbed by most of the materials forming the usual printed letters. If the radiated energy
 EMI14.3
 is not transmitted by a medium bearing the => ==, 1 = There thermosensitive, the reproduced document must allow these radiations to pass so that the exposure can be made through the posterior face of the document bearing the printed characters.



   The following examples illustrate the invention.
 EMI14.4
 



  An oraphic product is prepared by depositing on a paper support a composition containing gelatin and 3'-8tâ perchlorate; I-7-sët.ax; -4 '' - beuo2pyxiâ. otbiacar'ocyayaine. A document bearing prints was placed in contact with the uncoated side of the paper. The whole was exposed to radiation comprising infrared emitted by an infrared lamp, and a replica of the original document, bearing the number, was obtained. René printed text.
 EMI14.5
 



  3J12L ± 2: Res 1% a = s analogous to cexax 3 are obtained in Example 'using the following compounds: 1 to 10, 16 to 20, 23 and 24 to 31 from the list indicated above.
 EMI14.6
 



  .E: o #! '1E 3: A composition formed of gelatin and compound 13 is applied to a sheet of alut: iniur: 1, and one writes with a heating point on the back of the paper. An image is obtained in the heated areas.

Claims (1)

EMI15.1 t " ¯. (ià' fi ' .-- - D ' : REVEIJDICATIONS ' ,rr . r1 ' v ,1..-, :- [2 ,, .(r l B' ,1, à ]($µ ., ¯ I.- Produit thennographique comprenant un support et. un composé thermosensible caractérisé en ce que ce composé a pour fornule EMI15.2 dans lesquelles R'' désigne une liaison méthinique terminée par un noyau, hétérocyclique du type contenu dans les colorants cyanine 0 et conténant avantageusement cinq ou six chaînons un radical EMI15.3 - anilinovinzle, ru styryle################### ########HS désigne -une liaison néthini;psterBinée par un noyau. hétérocyclique du type contenu dans les colorants mérocyanine EMI15.4 ou un radical aï3.fLzdéne, z désigne un radical alcoyle éve.."ltueJ.1e- 5 r: EMI15.1 t "¯. (ià 'fi' .-- - D ': REVEIJDICATIONS', rr. r1 'v, 1 ..-,: - [2 ,,. (rl B', 1, to] ($ µ. , ¯ I.- Thermographic product comprising a support and. A thermosensitive compound characterized in that this compound has fornule EMI15.2 in which R '' denotes a methine bond terminated by a ring, heterocyclic of the type contained in the cyanine 0 dyes and advantageously containing five or six members a radical EMI15.3 - anilinovinzle, ru styryle ################### ######## HS denotes -a nethini bond; psterBinée by a nucleus. heterocyclic of the type contained in merocyanine dyes EMI15.4 or an aï3.fLzdene radical, z denotes a high alkyl radical .. "ltueJ.1e- 5 r: ent substitué ou acyle, X désigne un anion et Z représente 1?en- semble des atomes non métalliques nécessaires pour compléter un noyau hétérocyclique à cinq ou à six chaînons. ent substituted or acyl, X denotes an anion and Z represents the set of non-metallic atoms necessary to complete a five- or six-membered heterocyclic ring. 2.- Produit thermographique conforme à la revendication 1, caractérisé en ce que le dit composé correspond à l'une des for- 'suies suivantes : EMI15.5 <Desc/Clms Page number 16> EMI16.1 EMI16.2 dons lesquelles Q 1. 9 q 2 9 Q 3 i Î"% 4 J ",1 ez bzz repr6#o=tex les atoxoa non mé11iquos &Cess=4a pour c, ,.er un noyas À6troycqa. à cinq ou six chaSaons, n es-- un nosbre ::le à 4, m un aa'ra da 1 À 3, R repréaen-we un radical alcoylône ou ßcayl.^.acxy contenant de 1 à 8 atones à* cà=bon* ou un raiioù .-..ya:'" la t'or=18 (C5.-a.r,ylène- (Czr2) t- -0 où a a la raleur i à 8, t à 9 oz u 1 ou est ëga2 1 1 ou à 2, X reprit4rze un axucm, . 2.- thermographic product according to claim 1, characterized in that said compound corresponds to one of the following forms: EMI15.5 <Desc / Clms Page number 16> EMI16.1 EMI16.2 So which Q 1. 9 q 2 9 Q 3 i Î "% 4 J", 1 ez bzz repr6 # o = tex the non-me11ical atoxoa & Cess = 4a for c,, .er a nucleus À6troycqa. with five or six chaSaons, n es-- a nosbre :: le at 4, m un aa'ra da 1 to 3, R represents an alkyl radical or ßcayl. ^. acxy containing from 1 to 8 atones at * cà = good * or a raiioù .- .. ya: '"la t'or = 18 (C5.-ar, ylène- (Czr2) t- -0 where aa the value i to 8, t to 9 oz u 1 or is ëga2 1 1 or to 2, X reprit4rze an axucm,. un groupe alcoyle Nt ac.718, D, E, J, 2 et R 4 un groupe aryle ou ..100yle ou un ttose d'hydrocéne, 83 un groupe alcoyle, ale6ryle, arir-le au a.loo:c;y, a un groupe sai.3ino- vinyle ou aryle et a 6 et un groupe cyannj 3. - hodui ihsxaap'ciçwa cont'orme à la :NIV8ndioatiOl1 ' ou 2, caractérisé ea ce que le csonpcsi tbarmosonsible a pour foraale EMI16.3 EMI16.4 où 1 8,Y=bo1.. #1 1*s aiensiaation* donn'*s aux NY8%ld1oa\1ona 'pr8c'-i.n18.. z... <Desc/Clms Page number 17> EMI17.1 an alkyl group Nt ac.718, D, E, J, 2 and R 4 an aryl or .100yl group or a ttose of hydrocene, 83 an alkyl group, ale6ryl, arir-le at a.loo: c; y , has a sai.3ino- vinyl or aryl group and has 6 and a cyannj group 3. - hodui ihsxaap'ciçwa cont'orme to: NIV8ndioatiOl1 'or 2, characterized ao that the csonpcsi tbarmosonsible has foraale EMI16.3 EMI16.4 where 1 8, Y = bo1 .. # 1 1 * s aiensiaation * given to NY8% ld1oa \ 1ona 'pr8c'-i.n18 .. z ... <Desc / Clms Page number 17> EMI17.1 4* - Produit te:::-J::oë.p:;':n'1....e sonforne à 1.une quelconque des "evend.cnions précéete3, caractérise en 'ce que le composé thermosensible esc zp liùaé en CO...0:-.0 sur le support. 4 * - Product te ::: - J :: oë.p:; ': n'1 .... e sounds for 1. any of the above "evend.cnions3, characterized in' that the thermosensitive compound esc zp liùaé in CO ... 0: -. 0 on the support. 5 > - Produit t.tercogréip:::.i;u ,oor;..e à. l'une des reven- 3ica:o:.s 1 à 3, caractérisé e c# quo la cosposê thermosensible inpràgne la support. 5> - Product t.tercogréip :::. I; u, oor; .. e to. one of the claims 3ica: o: .s 1 to 3, characterized e c # quo the thermosensitive cosposê inpràgne the support. 6...- Produit th.er::::.ot:;=ê-;>1lilue conf'o:r# à. une des ='.1;'ruiica'tiona 1 à 4, '::é4"ë>c-:ârisé en cé que le composé i.Lt' a88nSîB est disperse t.2.rS une couche d'un S3u,0"...:.-^.^.'.. w% ,ôÉ2âiL'd.ßAS6B sur le support. EMI17.2 EMI17.3 6 ...- Product th.er::::.ot:;=ê-;>1lilue conf'o: r # to. one of = '. 1;' ruiica'tiona 1 to 4, ':: é4 "ë> c-: arized in that the compound i.Lt' a88nSîB is dispersed t.2.rS a layer of an S3u, 0 "...: .- ^. ^. '.. w%, ôÉ2âiL'd.ßAS6B on the support. EMI17.2 EMI17.3 7- Noiuît :er:a,;hiçuo conforme à l'une quelconque des :evendica;ioIlS précédentes, c.rc;:erisë en ce que le compose photosensible est le perchlorate do '--êH!yl-1-néthoxy-4',5*-l)enzo- 2-;:,= ia #hi ac bocyine. 7- Noiuît: er: a,; hiçuo in accordance with any one of: evendica; ioIlS preceding, c.rc;: erisë in that the photosensitive compound is the perchlorate do '--êH! Yl-1-nethoxy- 4 ', 5 * -1) enzo- 2 -;:, = ia #hi ac bocyine.
BE740042A 1968-10-09 1969-10-09 BE740042A (en)

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US76630768A 1968-10-09 1968-10-09

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Family Applications (10)

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BE738228A BE738228A (en) 1968-10-09 1969-08-29
BE738229A BE738229A (en) 1968-10-09 1969-08-29
BE738227A BE738227A (en) 1968-10-09 1969-08-29 Spectrally sensitized photographic emulsion
BE738226A BE738226A (en) 1968-10-09 1969-08-29
BE738230A BE738230A (en) 1968-10-09 1969-08-29
BE738225A BE738225A (en) 1968-10-09 1969-08-29 New nitrogenous heterocyclic organic compounds
BE740042A BE740042A (en) 1968-10-09 1969-10-09
BE740044A BE740044A (en) 1968-10-09 1969-10-09
BE740041A BE740041A (en) 1968-10-09 1969-10-09 Spectrally sensitized photographic emulsion
BE740043A BE740043A (en) 1968-10-09 1969-10-09

Family Applications Before (6)

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BE738228A BE738228A (en) 1968-10-09 1969-08-29
BE738229A BE738229A (en) 1968-10-09 1969-08-29
BE738227A BE738227A (en) 1968-10-09 1969-08-29 Spectrally sensitized photographic emulsion
BE738226A BE738226A (en) 1968-10-09 1969-08-29
BE738230A BE738230A (en) 1968-10-09 1969-08-29
BE738225A BE738225A (en) 1968-10-09 1969-08-29 New nitrogenous heterocyclic organic compounds

Family Applications After (3)

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BE740044A BE740044A (en) 1968-10-09 1969-10-09
BE740041A BE740041A (en) 1968-10-09 1969-10-09 Spectrally sensitized photographic emulsion
BE740043A BE740043A (en) 1968-10-09 1969-10-09

Country Status (8)

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US (1) US3615432A (en)
JP (4) JPS505584B1 (en)
BE (10) BE738228A (en)
BR (6) BR6913051D0 (en)
CH (3) CH530027A (en)
DE (5) DE1950746A1 (en)
FR (6) FR2020244A1 (en)
GB (4) GB1281566A (en)

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JPS525012A (en) * 1975-06-28 1977-01-14 Kubota Ltd Pipe joint
JPS5253093U (en) * 1975-10-13 1977-04-15
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US4410618A (en) * 1982-06-11 1983-10-18 Eastman Kodak Company Blocked photographic reagents
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Also Published As

Publication number Publication date
BE740041A (en) 1970-03-16
DE1950746A1 (en) 1970-04-09
BE738225A (en) 1970-03-02
GB1281567A (en) 1972-07-12
BE738230A (en) 1970-03-02
BR6913046D0 (en) 1973-01-25
US3615432A (en) 1971-10-26
DE1950735A1 (en) 1970-04-23
FR2020246A1 (en) 1970-07-10
JPS4930131B1 (en) 1974-08-10
BE738228A (en) 1970-03-02
JPS505584B1 (en) 1975-03-05
FR2020244A1 (en) 1970-07-10
BR6913050D0 (en) 1973-06-07
BE740044A (en) 1970-03-16
FR2020243A1 (en) 1970-07-10
FR2020245A1 (en) 1970-07-10
JPS4931127B1 (en) 1974-08-19
BR6913049D0 (en) 1973-01-25
FR2020247A1 (en) 1970-07-10
BE740043A (en) 1970-03-16
BR6913048D0 (en) 1973-01-25
BR6913051D0 (en) 1973-05-10
DE1950726C3 (en) 1982-02-04
DE1950779A1 (en) 1970-05-14
DE1950766B2 (en) 1971-03-18
CH517317A (en) 1971-12-31
BE738227A (en) 1970-03-02
FR2022244A1 (en) 1970-07-31
CH530027A (en) 1972-10-31
BE738226A (en) 1970-03-02
DE1950766A1 (en) 1970-04-16
GB1281566A (en) 1972-07-12
CH506096A (en) 1971-04-15
GB1276129A (en) 1972-06-01
DE1950726A1 (en) 1970-05-14
GB1281565A (en) 1972-07-12
JPS4910691B1 (en) 1974-03-12
BE738229A (en) 1970-03-02
DE1950757A1 (en) 1970-05-14
BR6913047D0 (en) 1973-01-25
DE1950726B2 (en) 1981-05-07

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